Women continue to be underrepresented in leadership positions within sport. As the number of women entering sport increases, a growing number of professionals recognize the inherent benefits of the mentoring relationship across a range of professional settings including sport (Bower, Hums, & Keedy, 2006; Grappendorf, Burton, & Lilienthal, 2007). Unfortunately, mentors are not always a viable option for women wanting to advance within leadership positions in sport. A primary reason for limited opportunities is the shortage of female in leadership positions within sport organizations creating a dearth of potential female mentors (Weaver & Chelladurai, 2002). Therefore, this paper explored the dynamics of the mentoring relationship between one professional organization (NAGWS) and potential career outcomes for women in sport. Specifically, how does NAGWS use group mentoring initiatives for girls and women in sport which may lead to potential advancement opportunities?